Thionyl Chloride → N-Methyl 4-Methoxybenzimidoyl Chloride

HRID 370909Notes

Reaction equation

HRID 370909 reaction equation
[CH3:1][NH:2][C:3](=O)[C:4]1[CH:9]=[CH:8][C:7]([O:10][CH3:11])=[CH:6][CH:5]=1.S(Cl)([Cl:15])=O>>[CH3:1][N:2]=[C:3]([Cl:15])[C:4]1[CH:9]=[CH:8][C:7]([O:10][CH3:11])=[CH:6][CH:5]=1

Participants

3

Reactant 2

HCID 24386Thionyl ChlorideHCID 3460314-methoxy-N-methylbenzamide

Product 1

HCID 12410495N-Methyl 4-Methoxybenzimidoyl ChlorideYield 76.7%

Procedure

N-Methyl 4-methoxybenzamide (13.95 g, 84.5 mmole) was placed in a 50 ml round bottom flask equipped with magnetic stirrer, heating mantle, condenser and base trap. Thionyl chloride (33 g, 278 mmole) was added. The reaction was stirred and heated at reflux until gas evolution ceased (three hours). The excess thionyl chloride was distilled at ca. 15 mm Hg, and the product distilled at 75°-80° C. (0.1 mm Hg) to yield 11.9 g (76%) of the title compound as a clear colorless liquid.

Workup

  1. customequipped with magnetic stirrer
  2. temperatureheating mantle, condenser and base trap
  3. temperatureheated
  4. temperatureat reflux until gas evolution
  5. custom(three hours)
  6. distillationThe excess thionyl chloride was distilled at ca. 15 mm Hg
  7. distillationthe product distilled at 75°-80° C. (0.1 mm Hg)

Sources & evidence

ORD record
ord-4883742856d94c599313418f15ed2269
Source dataset
uspto-grants-1985_07
Patent number
US04528382

Reaction notes

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